organic compounds
c]quinoline-5a(5H)-carboxylate
of methyl 1-methyl-3,5-diphenyl-7-tosyl-3,6,7,11b-tetrahydropyrazolo[4′,3′:5,6]pyrano[3,4-aCentre of Advanced Study in Crystallography and Biophysics, University of Madras, Guindy Campus, Chennai 600 025, India, bDepartment of Physics, Presidency College, Chennai 600 005, India, and cDepartment of Organic Chemistry, University of Madras, Guindy Campus, Chennai 600 025, India
*Correspondence e-mail: gunaunom@gmail.com
In the title compound, C35H31N3O5S, the piperidine ring adopts an with the methine C atom as the flap, and the pyran ring adopts a sofa conformation. The mean planes of these two rings are almost normal to one another, making a dihedral angle of 85.96 (5)°. The two phenyl rings, one attached to the pyrazole ring and the other to the pyran ring, are inclined to one another by 65.41 (11)°. They are inclined to the mean planes of the rings to which they are attached by 12.59 (11) and 70.09 (9)°, respectively. There is an intramolecular C—H⋯π interaction involving the tosylate methyl group and the phenyl ring attached to the pyrazole ring. In the crystal, molecules are linked by C—H⋯π interactions, forming ribbons parallel to (10-2). The ribbons are linked by slipped parallel π–π interactions involving inversion-related pyrazole rings [inter-centroid distance = 3.672 (2) Å], forming slabs parallel to (001). A preliminary report of this structure has been published [Bakthadoss et al. (2014). Eur. J. Org. Chem. pp. 1505–1513].
Keywords: crystal structure; sulfonamide; C—H⋯π interactions; Thrope–Ingold effect.
CCDC reference: 1034400
1. Related literature
For biological activity of sulfonamide compounds, see: Genç et al. (2008); Özbek et al. (2007); Briganti et al. (1997); Borne et al. (1974); De Clercq (2001). For details of the Thrope–Ingold effect, see: Bassindale (1984). For a preliminary report of this structure, see: Bakthadoss et al. (2014).
2. Experimental
2.1. Crystal data
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2.3. Refinement
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Data collection: APEX2 (Bruker, 2004); cell APEX2 and SAINT (Bruker, 2004); data reduction: SAINT and XPREP (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009) and Mercury (Macrae et al., 2008); software used to prepare material for publication: PLATON.
Supporting information
CCDC reference: 1034400
10.1107/S160053681402515X/su5015sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: 10.1107/S160053681402515X/su5015Isup2.hkl
Supporting information file. DOI: 10.1107/S160053681402515X/su5015Isup3.cml
A mixture of methyl (2E)-2-{[N-(2-formylphenyl)(4-methylbenzene) sulfonamido]methyl}-3-phenylprop-2-enoate (0.450 g, 1 mmol) and 3-methyl-1-phenyl-4,5-dihydro-1H-pyrazol-5-one (0.174 g, 1 mmol) was placed in a round bottom flask and heated at 453 K for 1 h. After completion of the reaction, as indicated by TLC, the crude product was washed with 5 ml of an ethylacetate/hexane mixture (ratio 1:49) which successfully provided the pure title product as a colourless solid in 96% yield (0.58 g). Diffraction quality crystals were obtained by slow evaporation from an ethyl acetate solution.
Atoms H10, H19 were located in a difference Fourier map and freely refined. The other C-bound H atoms were positioned geometrically and treated as riding atoms, with C—H = 0.93–0.97 Å and with Uiso(H) = 1.5Ueq(C) for methyl H atoms and = 1.2Ueq(C) for other H atoms.
Data collection: APEX2 (Bruker, 2004); cell
APEX2 and SAINT (Bruker, 2004); data reduction: SAINT and XPREP (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009) and Mercury (Macrae et al., 2008); software used to prepare material for publication: PLATON (Spek, 2009).The molecular structure of the title compound, with atom labelling. Displacement ellipsoids are drawn at the 30% probability level (H atoms have been omitted for clarity). A partial view along the b axis of the crystal packing of the title compound, showing the π-π interaction (red circles represent the centroids of the pyrazole rings; H atoms have been omitted for clarity). A view along the c axis of the crystal packing of the title compound, showing the C—H···π interactions as dashed lines (H atoms as silver balls; see Table 1 for details; H atoms not involved in these interactions have been omitted for clarity). |
C35H31N3O5S | Z = 2 |
Mr = 605.69 | F(000) = 636 |
Triclinic, P1 | Dx = 1.326 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 10.781 (5) Å | Cell parameters from 8834 reflections |
b = 11.682 (5) Å | θ = 2.1–31.2° |
c = 14.560 (5) Å | µ = 0.16 mm−1 |
α = 112.708 (5)° | T = 293 K |
β = 91.908 (5)° | Block, colourless |
γ = 113.180 (5)° | 0.25 × 0.20 × 0.20 mm |
V = 1517.5 (11) Å3 |
Bruker Kappa APEXII CCD diffractometer | 6308 independent reflections |
Radiation source: fine-focus sealed tube | 5070 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.028 |
ω and ϕ scan | θmax = 26.6°, θmin = 1.6° |
Absorption correction: multi-scan (SADABS; Bruker, 2004) | h = −13→13 |
Tmin = 0.979, Tmax = 0.983 | k = −14→14 |
23138 measured reflections | l = −18→18 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.043 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.118 | w = 1/[σ2(Fo2) + (0.0517P)2 + 0.4727P] where P = (Fo2 + 2Fc2)/3 |
S = 1.04 | (Δ/σ)max = 0.001 |
6308 reflections | Δρmax = 0.29 e Å−3 |
406 parameters | Δρmin = −0.46 e Å−3 |
0 restraints | Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0095 (12) |
C35H31N3O5S | γ = 113.180 (5)° |
Mr = 605.69 | V = 1517.5 (11) Å3 |
Triclinic, P1 | Z = 2 |
a = 10.781 (5) Å | Mo Kα radiation |
b = 11.682 (5) Å | µ = 0.16 mm−1 |
c = 14.560 (5) Å | T = 293 K |
α = 112.708 (5)° | 0.25 × 0.20 × 0.20 mm |
β = 91.908 (5)° |
Bruker Kappa APEXII CCD diffractometer | 6308 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2004) | 5070 reflections with I > 2σ(I) |
Tmin = 0.979, Tmax = 0.983 | Rint = 0.028 |
23138 measured reflections |
R[F2 > 2σ(F2)] = 0.043 | 0 restraints |
wR(F2) = 0.118 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.04 | Δρmax = 0.29 e Å−3 |
6308 reflections | Δρmin = −0.46 e Å−3 |
406 parameters |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | ||
H10 | 0.3360 (16) | 1.4361 (17) | 0.3161 (12) | 0.040 (4)* | |
H19 | 0.5740 (16) | 1.5341 (17) | 0.3206 (12) | 0.039 (4)* | |
S1 | 0.28913 (5) | 0.93229 (4) | 0.10089 (4) | 0.05837 (16) | |
O3 | 0.63192 (11) | 1.40325 (11) | 0.34307 (8) | 0.0427 (3) | |
N2 | 0.44250 (14) | 1.28179 (15) | 0.50555 (10) | 0.0451 (3) | |
N1 | 0.56158 (13) | 1.32792 (14) | 0.47097 (10) | 0.0408 (3) | |
O5 | 0.39810 (15) | 1.50993 (13) | 0.17850 (9) | 0.0585 (3) | |
C10 | 0.33680 (16) | 1.34586 (16) | 0.28908 (11) | 0.0383 (3) | |
C18 | 0.53403 (16) | 1.35576 (15) | 0.39247 (11) | 0.0381 (3) | |
C8 | 0.42521 (16) | 1.19731 (15) | 0.15787 (12) | 0.0428 (4) | |
H8A | 0.4420 | 1.1826 | 0.0901 | 0.051* | |
H8B | 0.4977 | 1.1919 | 0.1947 | 0.051* | |
C11 | 0.19167 (16) | 1.23858 (17) | 0.23342 (12) | 0.0428 (4) | |
C26 | 0.68408 (17) | 1.33323 (16) | 0.51560 (12) | 0.0434 (4) | |
N3 | 0.29016 (14) | 1.08531 (14) | 0.14857 (12) | 0.0519 (4) | |
C9 | 0.43402 (16) | 1.34228 (15) | 0.21259 (11) | 0.0374 (3) | |
C32 | 0.34569 (16) | 1.28201 (17) | 0.44719 (12) | 0.0415 (3) | |
C19 | 0.58361 (16) | 1.45108 (15) | 0.27642 (11) | 0.0378 (3) | |
C12 | 0.17045 (17) | 1.10761 (18) | 0.16377 (12) | 0.0463 (4) | |
C20 | 0.69474 (16) | 1.48845 (15) | 0.21891 (11) | 0.0405 (3) | |
C17 | 0.39844 (16) | 1.32776 (15) | 0.37384 (11) | 0.0373 (3) | |
C34 | 0.39288 (18) | 1.38461 (17) | 0.13379 (12) | 0.0471 (4) | |
C31 | 0.6898 (2) | 1.31935 (19) | 0.60547 (13) | 0.0534 (4) | |
H31 | 0.6142 | 1.3067 | 0.6361 | 0.064* | |
O4 | 0.35987 (19) | 1.31515 (16) | 0.04410 (10) | 0.0804 (5) | |
O1 | 0.33189 (16) | 0.90828 (14) | 0.00616 (10) | 0.0696 (4) | |
C21 | 0.7437 (2) | 1.61657 (19) | 0.21789 (15) | 0.0584 (5) | |
H21 | 0.7050 | 1.6760 | 0.2501 | 0.070* | |
C33 | 0.20231 (19) | 1.2383 (2) | 0.46483 (16) | 0.0623 (5) | |
H33A | 0.1976 | 1.2124 | 0.5202 | 0.093* | |
H33B | 0.1391 | 1.1607 | 0.4041 | 0.093* | |
H33C | 0.1779 | 1.3135 | 0.4815 | 0.093* | |
C5 | 0.4190 (2) | 0.95070 (16) | 0.18862 (14) | 0.0535 (4) | |
C25 | 0.75349 (19) | 1.40223 (17) | 0.17003 (14) | 0.0540 (4) | |
H25 | 0.7215 | 1.3154 | 0.1694 | 0.065* | |
O2 | 0.16039 (16) | 0.83495 (14) | 0.10388 (15) | 0.0914 (5) | |
C16 | 0.08020 (19) | 1.2695 (2) | 0.24679 (15) | 0.0574 (5) | |
H16 | 0.0947 | 1.3581 | 0.2915 | 0.069* | |
C23 | 0.9079 (2) | 1.5709 (2) | 0.12211 (15) | 0.0671 (6) | |
H23 | 0.9800 | 1.5988 | 0.0903 | 0.080* | |
C13 | 0.03616 (19) | 1.0084 (2) | 0.11023 (14) | 0.0599 (5) | |
H13 | 0.0207 | 0.9206 | 0.0631 | 0.072* | |
C30 | 0.8089 (2) | 1.3243 (2) | 0.64975 (16) | 0.0653 (5) | |
H30 | 0.8127 | 1.3152 | 0.7104 | 0.078* | |
C28 | 0.9133 (2) | 1.3542 (3) | 0.5160 (2) | 0.0762 (6) | |
H28 | 0.9890 | 1.3661 | 0.4855 | 0.091* | |
C14 | −0.0727 (2) | 1.0410 (3) | 0.12734 (16) | 0.0709 (6) | |
H14 | −0.1620 | 0.9738 | 0.0926 | 0.085* | |
C24 | 0.8596 (2) | 1.4436 (2) | 0.12183 (15) | 0.0648 (5) | |
H24 | 0.8983 | 1.3844 | 0.0891 | 0.078* | |
C29 | 0.9205 (2) | 1.3424 (2) | 0.60559 (18) | 0.0706 (6) | |
H29 | 1.0003 | 1.3465 | 0.6360 | 0.085* | |
C27 | 0.7955 (2) | 1.3489 (2) | 0.46962 (17) | 0.0639 (5) | |
H27 | 0.7917 | 1.3558 | 0.4082 | 0.077* | |
C4 | 0.5298 (2) | 0.9284 (2) | 0.15784 (17) | 0.0696 (6) | |
H4 | 0.5400 | 0.9094 | 0.0911 | 0.084* | |
C2 | 0.6146 (3) | 0.9648 (2) | 0.32640 (18) | 0.0749 (6) | |
C6 | 0.4065 (3) | 0.9812 (2) | 0.28845 (17) | 0.0773 (7) | |
H6 | 0.3319 | 0.9970 | 0.3099 | 0.093* | |
C15 | −0.0524 (2) | 1.1702 (3) | 0.19444 (18) | 0.0717 (6) | |
H15 | −0.1270 | 1.1911 | 0.2048 | 0.086* | |
C22 | 0.8497 (2) | 1.6572 (2) | 0.16937 (18) | 0.0731 (6) | |
H22 | 0.8814 | 1.7433 | 0.1689 | 0.088* | |
C1 | 0.7210 (4) | 0.9729 (3) | 0.4012 (2) | 0.1103 (10) | |
H1A | 0.7904 | 0.9537 | 0.3676 | 0.165* | |
H1B | 0.6772 | 0.9062 | 0.4272 | 0.165* | |
H1C | 0.7633 | 1.0639 | 0.4566 | 0.165* | |
C3 | 0.6255 (3) | 0.9343 (3) | 0.2266 (2) | 0.0811 (7) | |
H3 | 0.6994 | 0.9173 | 0.2051 | 0.097* | |
C7 | 0.5029 (3) | 0.9882 (3) | 0.35505 (18) | 0.0877 (8) | |
H7 | 0.4935 | 1.0093 | 0.4221 | 0.105* | |
C35 | 0.3590 (3) | 1.5611 (3) | 0.1114 (2) | 0.0913 (8) | |
H35B | 0.3666 | 1.6518 | 0.1513 | 0.137* | |
H35A | 0.2653 | 1.4999 | 0.0741 | 0.137* | |
H35C | 0.4193 | 1.5652 | 0.0645 | 0.137* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0555 (3) | 0.0336 (2) | 0.0674 (3) | 0.00953 (19) | 0.0169 (2) | 0.0141 (2) |
O3 | 0.0370 (6) | 0.0510 (6) | 0.0478 (6) | 0.0183 (5) | 0.0128 (5) | 0.0297 (5) |
N2 | 0.0434 (8) | 0.0582 (8) | 0.0469 (7) | 0.0262 (7) | 0.0174 (6) | 0.0310 (7) |
N1 | 0.0384 (7) | 0.0492 (7) | 0.0440 (7) | 0.0221 (6) | 0.0125 (6) | 0.0260 (6) |
O5 | 0.0812 (9) | 0.0553 (7) | 0.0515 (7) | 0.0362 (7) | 0.0097 (6) | 0.0295 (6) |
C10 | 0.0407 (8) | 0.0399 (8) | 0.0391 (8) | 0.0208 (7) | 0.0108 (6) | 0.0186 (6) |
C18 | 0.0402 (8) | 0.0386 (7) | 0.0391 (8) | 0.0183 (7) | 0.0116 (6) | 0.0192 (6) |
C8 | 0.0405 (9) | 0.0353 (8) | 0.0470 (9) | 0.0120 (7) | 0.0154 (7) | 0.0169 (7) |
C11 | 0.0390 (9) | 0.0544 (9) | 0.0410 (8) | 0.0204 (7) | 0.0103 (7) | 0.0266 (7) |
C26 | 0.0420 (9) | 0.0413 (8) | 0.0499 (9) | 0.0203 (7) | 0.0061 (7) | 0.0211 (7) |
N3 | 0.0405 (8) | 0.0370 (7) | 0.0665 (9) | 0.0105 (6) | 0.0173 (7) | 0.0174 (7) |
C9 | 0.0388 (8) | 0.0355 (7) | 0.0370 (7) | 0.0141 (6) | 0.0097 (6) | 0.0171 (6) |
C32 | 0.0421 (9) | 0.0495 (9) | 0.0411 (8) | 0.0243 (7) | 0.0150 (7) | 0.0227 (7) |
C19 | 0.0422 (9) | 0.0343 (7) | 0.0374 (7) | 0.0157 (7) | 0.0091 (6) | 0.0171 (6) |
C12 | 0.0392 (9) | 0.0543 (9) | 0.0416 (8) | 0.0146 (7) | 0.0103 (7) | 0.0231 (7) |
C20 | 0.0402 (8) | 0.0360 (7) | 0.0373 (8) | 0.0096 (6) | 0.0067 (6) | 0.0156 (6) |
C17 | 0.0383 (8) | 0.0390 (7) | 0.0379 (7) | 0.0193 (6) | 0.0110 (6) | 0.0175 (6) |
C34 | 0.0473 (10) | 0.0483 (9) | 0.0432 (9) | 0.0157 (8) | 0.0085 (7) | 0.0232 (7) |
C31 | 0.0554 (11) | 0.0603 (11) | 0.0497 (10) | 0.0301 (9) | 0.0089 (8) | 0.0245 (8) |
O4 | 0.1224 (14) | 0.0725 (9) | 0.0388 (7) | 0.0412 (9) | 0.0013 (8) | 0.0200 (7) |
O1 | 0.0846 (10) | 0.0541 (8) | 0.0490 (7) | 0.0274 (7) | 0.0122 (7) | 0.0056 (6) |
C21 | 0.0624 (12) | 0.0466 (9) | 0.0712 (12) | 0.0200 (9) | 0.0212 (10) | 0.0340 (9) |
C33 | 0.0481 (11) | 0.0974 (15) | 0.0655 (12) | 0.0370 (11) | 0.0260 (9) | 0.0524 (11) |
C5 | 0.0718 (12) | 0.0342 (8) | 0.0576 (10) | 0.0222 (8) | 0.0291 (9) | 0.0231 (7) |
C25 | 0.0528 (10) | 0.0390 (8) | 0.0604 (10) | 0.0135 (8) | 0.0218 (8) | 0.0181 (8) |
O2 | 0.0651 (10) | 0.0440 (8) | 0.1374 (15) | 0.0041 (7) | 0.0300 (10) | 0.0326 (9) |
C16 | 0.0482 (11) | 0.0734 (12) | 0.0613 (11) | 0.0323 (10) | 0.0156 (9) | 0.0337 (10) |
C23 | 0.0573 (12) | 0.0717 (13) | 0.0573 (11) | 0.0091 (10) | 0.0221 (9) | 0.0326 (10) |
C13 | 0.0459 (10) | 0.0661 (12) | 0.0472 (10) | 0.0098 (9) | 0.0079 (8) | 0.0202 (9) |
C30 | 0.0686 (13) | 0.0733 (13) | 0.0588 (11) | 0.0372 (11) | −0.0015 (10) | 0.0284 (10) |
C28 | 0.0486 (12) | 0.0986 (17) | 0.1131 (19) | 0.0394 (12) | 0.0253 (12) | 0.0689 (15) |
C14 | 0.0384 (10) | 0.0953 (17) | 0.0600 (12) | 0.0134 (10) | 0.0042 (9) | 0.0325 (12) |
C24 | 0.0549 (11) | 0.0579 (11) | 0.0605 (11) | 0.0144 (9) | 0.0250 (9) | 0.0149 (9) |
C29 | 0.0519 (12) | 0.0750 (13) | 0.0912 (15) | 0.0313 (11) | −0.0010 (11) | 0.0400 (12) |
C27 | 0.0512 (11) | 0.0893 (14) | 0.0827 (14) | 0.0388 (11) | 0.0244 (10) | 0.0591 (12) |
C4 | 0.0756 (14) | 0.0833 (14) | 0.0634 (12) | 0.0378 (12) | 0.0333 (11) | 0.0405 (11) |
C2 | 0.1020 (18) | 0.0482 (11) | 0.0754 (14) | 0.0260 (11) | 0.0109 (13) | 0.0356 (10) |
C6 | 0.123 (2) | 0.0769 (14) | 0.0718 (14) | 0.0663 (15) | 0.0543 (14) | 0.0453 (12) |
C15 | 0.0422 (11) | 0.1032 (18) | 0.0780 (14) | 0.0350 (12) | 0.0131 (10) | 0.0444 (14) |
C22 | 0.0742 (14) | 0.0611 (12) | 0.0874 (15) | 0.0142 (11) | 0.0269 (12) | 0.0508 (12) |
C1 | 0.146 (3) | 0.0780 (17) | 0.106 (2) | 0.0447 (18) | −0.0054 (19) | 0.0468 (16) |
C3 | 0.0771 (16) | 0.0935 (17) | 0.0934 (17) | 0.0399 (14) | 0.0352 (13) | 0.0570 (14) |
C7 | 0.155 (3) | 0.0794 (15) | 0.0605 (13) | 0.0726 (18) | 0.0419 (15) | 0.0387 (12) |
C35 | 0.134 (2) | 0.0933 (17) | 0.0816 (16) | 0.0638 (17) | 0.0154 (15) | 0.0578 (14) |
S1—O2 | 1.4217 (16) | C33—H33B | 0.9600 |
S1—O1 | 1.4279 (15) | C33—H33C | 0.9600 |
S1—N3 | 1.6442 (16) | C5—C4 | 1.373 (3) |
S1—C5 | 1.752 (2) | C5—C6 | 1.382 (3) |
O3—C18 | 1.3552 (18) | C25—C24 | 1.384 (2) |
O3—C19 | 1.4627 (18) | C25—H25 | 0.9300 |
N2—C32 | 1.325 (2) | C16—C15 | 1.382 (3) |
N2—N1 | 1.3784 (18) | C16—H16 | 0.9300 |
N1—C18 | 1.3567 (19) | C23—C24 | 1.367 (3) |
N1—C26 | 1.420 (2) | C23—C22 | 1.369 (3) |
O5—C34 | 1.329 (2) | C23—H23 | 0.9300 |
O5—C35 | 1.453 (2) | C13—C14 | 1.372 (3) |
C10—C11 | 1.504 (2) | C13—H13 | 0.9300 |
C10—C17 | 1.506 (2) | C30—C29 | 1.365 (3) |
C10—C9 | 1.555 (2) | C30—H30 | 0.9300 |
C10—H10 | 0.977 (16) | C28—C29 | 1.367 (3) |
C18—C17 | 1.359 (2) | C28—C27 | 1.385 (3) |
C8—N3 | 1.483 (2) | C28—H28 | 0.9300 |
C8—C9 | 1.529 (2) | C14—C15 | 1.367 (3) |
C8—H8A | 0.9700 | C14—H14 | 0.9300 |
C8—H8B | 0.9700 | C24—H24 | 0.9300 |
C11—C16 | 1.384 (2) | C29—H29 | 0.9300 |
C11—C12 | 1.390 (2) | C27—H27 | 0.9300 |
C26—C27 | 1.378 (3) | C4—C3 | 1.376 (3) |
C26—C31 | 1.382 (2) | C4—H4 | 0.9300 |
N3—C12 | 1.422 (2) | C2—C3 | 1.377 (3) |
C9—C34 | 1.528 (2) | C2—C7 | 1.380 (4) |
C9—C19 | 1.567 (2) | C2—C1 | 1.505 (4) |
C32—C17 | 1.411 (2) | C6—C7 | 1.354 (4) |
C32—C33 | 1.491 (2) | C6—H6 | 0.9300 |
C19—C20 | 1.505 (2) | C15—H15 | 0.9300 |
C19—H19 | 0.983 (16) | C22—H22 | 0.9300 |
C12—C13 | 1.398 (3) | C1—H1A | 0.9600 |
C20—C25 | 1.379 (2) | C1—H1B | 0.9600 |
C20—C21 | 1.384 (2) | C1—H1C | 0.9600 |
C34—O4 | 1.189 (2) | C3—H3 | 0.9300 |
C31—C30 | 1.387 (3) | C7—H7 | 0.9300 |
C31—H31 | 0.9300 | C35—H35B | 0.9600 |
C21—C22 | 1.384 (3) | C35—H35A | 0.9600 |
C21—H21 | 0.9300 | C35—H35C | 0.9600 |
C33—H33A | 0.9600 | ||
O2—S1—O1 | 119.29 (10) | H33A—C33—H33B | 109.5 |
O2—S1—N3 | 108.19 (9) | C32—C33—H33C | 109.5 |
O1—S1—N3 | 108.89 (8) | H33A—C33—H33C | 109.5 |
O2—S1—C5 | 108.09 (11) | H33B—C33—H33C | 109.5 |
O1—S1—C5 | 107.78 (9) | C4—C5—C6 | 119.6 (2) |
N3—S1—C5 | 103.47 (8) | C4—C5—S1 | 120.53 (15) |
C18—O3—C19 | 111.44 (12) | C6—C5—S1 | 119.75 (17) |
C32—N2—N1 | 105.70 (12) | C20—C25—C24 | 120.66 (17) |
C18—N1—N2 | 109.14 (12) | C20—C25—H25 | 119.7 |
C18—N1—C26 | 131.38 (13) | C24—C25—H25 | 119.7 |
N2—N1—C26 | 119.42 (12) | C15—C16—C11 | 120.7 (2) |
C34—O5—C35 | 116.36 (16) | C15—C16—H16 | 119.6 |
C11—C10—C17 | 115.19 (13) | C11—C16—H16 | 119.6 |
C11—C10—C9 | 109.36 (13) | C24—C23—C22 | 119.68 (18) |
C17—C10—C9 | 106.39 (12) | C24—C23—H23 | 120.2 |
C11—C10—H10 | 107.5 (10) | C22—C23—H23 | 120.2 |
C17—C10—H10 | 109.8 (9) | C14—C13—C12 | 119.8 (2) |
C9—C10—H10 | 108.4 (9) | C14—C13—H13 | 120.1 |
O3—C18—N1 | 122.47 (14) | C12—C13—H13 | 120.1 |
O3—C18—C17 | 127.94 (14) | C29—C30—C31 | 120.89 (19) |
N1—C18—C17 | 109.59 (13) | C29—C30—H30 | 119.6 |
N3—C8—C9 | 113.72 (13) | C31—C30—H30 | 119.6 |
N3—C8—H8A | 108.8 | C29—C28—C27 | 121.4 (2) |
C9—C8—H8A | 108.8 | C29—C28—H28 | 119.3 |
N3—C8—H8B | 108.8 | C27—C28—H28 | 119.3 |
C9—C8—H8B | 108.8 | C15—C14—C13 | 121.25 (19) |
H8A—C8—H8B | 107.7 | C15—C14—H14 | 119.4 |
C16—C11—C12 | 119.56 (16) | C13—C14—H14 | 119.4 |
C16—C11—C10 | 121.39 (16) | C23—C24—C25 | 120.4 (2) |
C12—C11—C10 | 118.99 (14) | C23—C24—H24 | 119.8 |
C27—C26—C31 | 119.75 (16) | C25—C24—H24 | 119.8 |
C27—C26—N1 | 121.13 (15) | C30—C29—C28 | 119.08 (19) |
C31—C26—N1 | 119.11 (15) | C30—C29—H29 | 120.5 |
C12—N3—C8 | 122.18 (14) | C28—C29—H29 | 120.5 |
C12—N3—S1 | 124.35 (11) | C26—C27—C28 | 119.28 (19) |
C8—N3—S1 | 112.69 (11) | C26—C27—H27 | 120.4 |
C34—C9—C8 | 109.29 (13) | C28—C27—H27 | 120.4 |
C34—C9—C10 | 109.65 (13) | C5—C4—C3 | 119.4 (2) |
C8—C9—C10 | 110.66 (12) | C5—C4—H4 | 120.3 |
C34—C9—C19 | 109.12 (12) | C3—C4—H4 | 120.3 |
C8—C9—C19 | 111.53 (13) | C3—C2—C7 | 117.4 (2) |
C10—C9—C19 | 106.54 (12) | C3—C2—C1 | 121.1 (3) |
N2—C32—C17 | 111.64 (14) | C7—C2—C1 | 121.4 (2) |
N2—C32—C33 | 119.83 (14) | C7—C6—C5 | 119.9 (2) |
C17—C32—C33 | 128.53 (15) | C7—C6—H6 | 120.1 |
O3—C19—C20 | 106.54 (12) | C5—C6—H6 | 120.1 |
O3—C19—C9 | 109.95 (11) | C14—C15—C16 | 119.4 (2) |
C20—C19—C9 | 117.66 (12) | C14—C15—H15 | 120.3 |
O3—C19—H19 | 107.2 (9) | C16—C15—H15 | 120.3 |
C20—C19—H19 | 109.9 (9) | C23—C22—C21 | 120.24 (18) |
C9—C19—H19 | 105.2 (10) | C23—C22—H22 | 119.9 |
C11—C12—C13 | 119.26 (17) | C21—C22—H22 | 119.9 |
C11—C12—N3 | 116.79 (15) | C2—C1—H1A | 109.5 |
C13—C12—N3 | 123.90 (17) | C2—C1—H1B | 109.5 |
C25—C20—C21 | 118.44 (16) | H1A—C1—H1B | 109.5 |
C25—C20—C19 | 122.73 (14) | C2—C1—H1C | 109.5 |
C21—C20—C19 | 118.79 (15) | H1A—C1—H1C | 109.5 |
C18—C17—C32 | 103.92 (13) | H1B—C1—H1C | 109.5 |
C18—C17—C10 | 121.65 (13) | C4—C3—C2 | 121.6 (2) |
C32—C17—C10 | 134.42 (14) | C4—C3—H3 | 119.2 |
O4—C34—O5 | 123.95 (16) | C2—C3—H3 | 119.2 |
O4—C34—C9 | 124.90 (16) | C6—C7—C2 | 122.0 (2) |
O5—C34—C9 | 111.15 (13) | C6—C7—H7 | 119.0 |
C26—C31—C30 | 119.63 (18) | C2—C7—H7 | 119.0 |
C26—C31—H31 | 120.2 | O5—C35—H35B | 109.5 |
C30—C31—H31 | 120.2 | O5—C35—H35A | 109.5 |
C20—C21—C22 | 120.60 (19) | H35B—C35—H35A | 109.5 |
C20—C21—H21 | 119.7 | O5—C35—H35C | 109.5 |
C22—C21—H21 | 119.7 | H35B—C35—H35C | 109.5 |
C32—C33—H33A | 109.5 | H35A—C35—H35C | 109.5 |
C32—C33—H33B | 109.5 | ||
C32—N2—N1—C18 | 0.31 (17) | O3—C18—C17—C10 | 0.9 (2) |
C32—N2—N1—C26 | −177.06 (14) | N1—C18—C17—C10 | −178.65 (13) |
C19—O3—C18—N1 | −168.50 (13) | N2—C32—C17—C18 | −0.31 (18) |
C19—O3—C18—C17 | 12.0 (2) | C33—C32—C17—C18 | 179.12 (18) |
N2—N1—C18—O3 | 179.90 (13) | N2—C32—C17—C10 | 178.67 (16) |
C26—N1—C18—O3 | −3.2 (3) | C33—C32—C17—C10 | −1.9 (3) |
N2—N1—C18—C17 | −0.52 (17) | C11—C10—C17—C18 | 142.60 (15) |
C26—N1—C18—C17 | 176.42 (15) | C9—C10—C17—C18 | 21.25 (19) |
C17—C10—C11—C16 | 107.29 (17) | C11—C10—C17—C32 | −36.2 (2) |
C9—C10—C11—C16 | −132.99 (15) | C9—C10—C17—C32 | −157.59 (17) |
C17—C10—C11—C12 | −75.64 (18) | C35—O5—C34—O4 | 0.7 (3) |
C9—C10—C11—C12 | 44.08 (18) | C35—O5—C34—C9 | −179.09 (17) |
C18—N1—C26—C27 | −11.1 (3) | C8—C9—C34—O4 | −0.3 (2) |
N2—N1—C26—C27 | 165.55 (16) | C10—C9—C34—O4 | −121.7 (2) |
C18—N1—C26—C31 | 170.30 (16) | C19—C9—C34—O4 | 121.9 (2) |
N2—N1—C26—C31 | −13.0 (2) | C8—C9—C34—O5 | 179.48 (13) |
C9—C8—N3—C12 | 15.9 (2) | C10—C9—C34—O5 | 58.02 (17) |
C9—C8—N3—S1 | −173.73 (11) | C19—C9—C34—O5 | −58.32 (18) |
O2—S1—N3—C12 | −15.17 (18) | C27—C26—C31—C30 | 1.4 (3) |
O1—S1—N3—C12 | 115.88 (15) | N1—C26—C31—C30 | 179.97 (16) |
C5—S1—N3—C12 | −129.68 (15) | C25—C20—C21—C22 | −0.4 (3) |
O2—S1—N3—C8 | 174.75 (13) | C19—C20—C21—C22 | 177.39 (18) |
O1—S1—N3—C8 | −54.20 (15) | O2—S1—C5—C4 | 124.05 (17) |
C5—S1—N3—C8 | 60.24 (14) | O1—S1—C5—C4 | −6.13 (18) |
N3—C8—C9—C34 | −92.95 (16) | N3—S1—C5—C4 | −121.37 (16) |
N3—C8—C9—C10 | 27.89 (18) | O2—S1—C5—C6 | −52.72 (18) |
N3—C8—C9—C19 | 146.30 (14) | O1—S1—C5—C6 | 177.09 (15) |
C11—C10—C9—C34 | 64.66 (16) | N3—S1—C5—C6 | 61.85 (16) |
C17—C10—C9—C34 | −170.33 (12) | C21—C20—C25—C24 | 0.5 (3) |
C11—C10—C9—C8 | −55.97 (16) | C19—C20—C25—C24 | −177.17 (17) |
C17—C10—C9—C8 | 69.04 (15) | C12—C11—C16—C15 | 2.4 (3) |
C11—C10—C9—C19 | −177.37 (12) | C10—C11—C16—C15 | 179.42 (17) |
C17—C10—C9—C19 | −52.37 (15) | C11—C12—C13—C14 | −0.4 (3) |
N1—N2—C32—C17 | 0.00 (18) | N3—C12—C13—C14 | −177.57 (17) |
N1—N2—C32—C33 | −179.48 (16) | C26—C31—C30—C29 | −0.2 (3) |
C18—O3—C19—C20 | −174.85 (12) | C12—C13—C14—C15 | 1.5 (3) |
C18—O3—C19—C9 | −46.32 (16) | C22—C23—C24—C25 | −0.8 (3) |
C34—C9—C19—O3 | −172.63 (12) | C20—C25—C24—C23 | 0.1 (3) |
C8—C9—C19—O3 | −51.79 (16) | C31—C30—C29—C28 | −0.6 (3) |
C10—C9—C19—O3 | 69.06 (15) | C27—C28—C29—C30 | 0.3 (4) |
C34—C9—C19—C20 | −50.48 (18) | C31—C26—C27—C28 | −1.7 (3) |
C8—C9—C19—C20 | 70.36 (16) | N1—C26—C27—C28 | 179.71 (19) |
C10—C9—C19—C20 | −168.78 (13) | C29—C28—C27—C26 | 0.9 (4) |
C16—C11—C12—C13 | −1.5 (2) | C6—C5—C4—C3 | 1.2 (3) |
C10—C11—C12—C13 | −178.65 (14) | S1—C5—C4—C3 | −175.61 (17) |
C16—C11—C12—N3 | 175.88 (15) | C4—C5—C6—C7 | −0.4 (3) |
C10—C11—C12—N3 | −1.3 (2) | S1—C5—C6—C7 | 176.45 (18) |
C8—N3—C12—C11 | −31.4 (2) | C13—C14—C15—C16 | −0.7 (3) |
S1—N3—C12—C11 | 159.43 (13) | C11—C16—C15—C14 | −1.3 (3) |
C8—N3—C12—C13 | 145.87 (17) | C24—C23—C22—C21 | 0.9 (3) |
S1—N3—C12—C13 | −23.3 (2) | C20—C21—C22—C23 | −0.3 (3) |
O3—C19—C20—C25 | 48.67 (19) | C5—C4—C3—C2 | −1.3 (4) |
C9—C19—C20—C25 | −75.2 (2) | C7—C2—C3—C4 | 0.6 (3) |
O3—C19—C20—C21 | −129.00 (16) | C1—C2—C3—C4 | −179.1 (2) |
C9—C19—C20—C21 | 107.12 (17) | C5—C6—C7—C2 | −0.4 (4) |
O3—C18—C17—C32 | −179.96 (15) | C3—C2—C7—C6 | 0.3 (4) |
N1—C18—C17—C32 | 0.49 (17) | C1—C2—C7—C6 | 180.0 (2) |
Cg4, Cg6 and Cg7 are the centroids of rings C2–C7, C20–C25 and C26–C31, respectively. |
D—H···A | D—H | H···A | D···A | D—H···A |
C1—H1C···Cg7 | 0.96 | 2.80 | 3.682 (4) | 154 |
C29—H29···Cg6i | 0.93 | 2.94 | 3.734 (3) | 144 |
C35—H35B···Cg4ii | 0.96 | 2.97 | 3.853 (4) | 154 |
Symmetry codes: (i) −x+2, −y+3, −z+1; (ii) x, y+1, z. |
Cg4, Cg6 and Cg7 are the centroids of rings C2–C7, C20–C25 and C26–C31, respectively. |
D—H···A | D—H | H···A | D···A | D—H···A |
C1—H1C···Cg7 | 0.96 | 2.80 | 3.682 (4) | 154 |
C29—H29···Cg6i | 0.93 | 2.94 | 3.734 (3) | 144 |
C35—H35B···Cg4ii | 0.96 | 2.97 | 3.853 (4) | 154 |
Symmetry codes: (i) −x+2, −y+3, −z+1; (ii) x, y+1, z. |
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This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
Sulfonamides are widely used as antimicrobial (Genç et al., 2008; Özbek et al., 2007), antifungal (Briganti et al., 1997), anti-inflammatory (Borne et al., 1974) and antiviral agents as well as HIV protease inhibitors (De Clercq et al., 2001). In view of their importance, a series of such compounds were synthesized and the crystal structure of the title compound was briefly reported (Bakthadoss et al., 2014). Herein we report on the full details of the crystal structure of the title compound.
The molecular structure of the title compound is shown in Fig. 1. Atom S1 has a distorted tetrahedral geometry, with the O1—S1—O2 [119.33 (1)°] and N3—S1—C5 [103.46 (1)°] bond angles deviating from the ideal tetrahedral values which is attributed to the Thrope-Ingold effect (Bassindale et al., 1984). The sum of the bond angles around atom N3 (359.22 (2)°) indicates that N3 is sp2 hybridized. The pyridine ring (N3/C8—C12) adopts an envelop conformation with atom C10 as the flap; it is displaced by -0.352 (2) Å from the mean formed by the remaining ring atoms. The pyran ring (C9/C10/C17/C18/O3/C19) adopts a sofa conformation [puckering parameters: q2 = 0.434 (2) Å, q3 = 0.358 (2) Å, ϕ2 = -19.64 (22) °]. The mean planes of these two rings are almost normal to one another with a dihedral angle of 85.96 (5)°. The two different phenyl rings (C26-C31 and C20-C25), attached to the pyrazole (N1/N2/C32/C17/C18) and pyran rings, respectively, are inclined to the mean planes of the rings to which they are attached by 12.59 (11) and 70.09 (9) °, respectively. They are inclined to one another by 65.41 (11) °. There is an intramolecular C-H···π interaction (Table 1) involving the tosylate methyl group, C1, and the phenyl ring (C26-C31) attached to the pyrazole ring.
In the crystal, molecules are linked by C-H···π interactions (Table 1) forming ribbons lying parallel to (102); see Fig. 2. The ribbons are linked via slipped parallel π-π interactions involving inversion related pyrazole rings [Fig. 3; Cg1···Cg1i = 3.672((2) Å; normal distance = 3.565 (1) Å, slippage = 0.882 Å; Cg1 centroid of ring (N1/N2/C18/C17/C32); symmetry code: (i) -x+1, -y+3, -z+1] forming slabs parallel to (001).